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Pyrrolidine-3-carboxylic Acids as Endothelin Antagonists. 4. Side Chain Conformational Restriction Leads to ETB Selectivity

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Metabolic Disease Research and Drug Analysis Department, Pharmaceutical Products Research Division, Abbott Laboratories, Abbott Park, Illinois 60064-6098
Cite this: J. Med. Chem. 1999, 42, 18, 3668–3678
Publication Date (Web):August 13, 1999
https://doi.org/10.1021/jm990170q
Copyright © 1999 American Chemical Society

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    Abstract

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    When the dialkylacetamide side chain of the ETA-selective antagonist ABT-627 is replaced with a 2,6-dialkylacetanilide, the resultant analogues show a complete reversal of receptor selectivity, preferring ETB over ETA. By optimizing the aniline substitution pattern, as well as the alkoxy group on the 2-aryl substituent, it is possible to prepare antagonists with subnanomolar affinity for ETB and with selectivities in excess of 4000-fold. A number of these compounds also show promising pharmacokinetic profiles; a useful balance of properties is found in A-192621 (38). Pharmacology studies with A-192621 serve to reveal the role of the ETB receptor in modulating blood pressure; the observed hypertensive response to persistent ETB blockade is consistent with previous postulates and indicates that ETB-selective antagonists may not be suitable as agents for long-term systemic therapy.

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    *

     Address correspondence to T. W. von Geldern, D-47H/AP10-LL-12E, Abbott Laboratories, 100 Abbott Park Rd; Abbott Park, IL 60064-6098. E-mail:  [email protected].

     Current address:  Amgen Inc., Thousand Oaks, CA 91320.

     Department of Drug Analysis.

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